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Prepare dough: Combine milk, shortening, sugar, and salt in a small saucepan over medium heat. Cook and stir until shortening melts and sugar dissolves. Remove from heat and let cool to lukewarm, 110 degrees F (43 degrees C).
Sprinkle yeast into the cooled dough mixture and let sit until foamy.
Transfer mixture to a large bowl and stir in flour to form a dough. Knead until smooth; cover and let rise 30 minutes.
Heat oil in a deep fryer or large saucepan to 375 degrees F (190 degrees C). Roll out 2-inch balls of dough into thin sheets; fry in hot oil until puffed and golden, about 1 to 2 minutes per side.
Drain on paper towels.
Prepare topping: Combine sugar and cinnamon in a bowl.
Sprinkle topping over warm elephant ears and serve.